N-substituiran 2-fenilimidazol kot substrat za katalitsko funkcionalizacijo C-H vezi

Močnik, Žiga (author), Požgan, Franc (mentor)

V diplomskem delu sem opisal postopek priprave N-funkcionaliziranih 2-fenil-1H-imidazolov in njihovo orto funkcionalizacijo preko C–H aktivacije v prisotnosti rutenijevih katalizatorjev. Predstavil sem lastnosti 2-fenilimidazola, pripravo N-funkcionaliziranih 2-fenilimidazolov, klasične reakcije križnega spajanja in katalitsko direktno funkcionalizacijo s pomočjo usmerjajočih skupin. Z eksperimentalnim delom sem želel ugotoviti vpliv prisotnosti različnih funkcionalnih skupin na imidazolu pri direktni C–H funkcionalizaciji. V prvi stopnji sem po postopkih iz literature pripravil N-metil, N-etil, N-butil, N-benzil in N-piridilmetil 2-fenil-1H-imidazole. Te produkte sem nato uporabil kot substrate za reakcijo s klorobenzenom v prisotnosi [Ru(p-cimen)Cl$_2$]$_2$ kot katalizatorja. Z namenom optimizacije reakcijskih pogojev sem spreminjal topilo in dodatek ligandov KOPiv in PPh$_3$. Ugotovil sem, da reakcije najbolje potečejo v vodi, dodatek ligandov pa ni potreben. Substituent na imidazolskem substratu pa vpliva na razmerje med mono- in di-substituiranima produktoma.

• Language: Slovenian
• Keywords: N-substituiran 2-fenilimidazol, C–H funkcionalizacija, usmerjajoča skupina, rutenijev katalizator
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2024
• PID: 20.500.12556/RUL-160708
• COBISS.SI-ID: 210971651
• Publication date in RUL: 03.09.2024

Secondary language

• Language: English
• Title: N-substituted 2-phenylimidazole as a substrate in the catalytic C-H bond functionalization

Abstract

In my thesis, I described the synthesis of N-functionalized 2-pheny-1H-imidazoles and their ortho functionalization via C–H activation with a ruthenium catalyst. I presented the properties of 2-phenylimidazole, synthesis of N-functionalized 2-phenylimidazoles, classic cross coupling reactions and catalytic direct functionalization aided by directing groups, and mechanism of ruthenium-catalyzed reactions. With my experiments I wanted to study the influence of different functional groups on imidazole for direct C–H functionalization. In the first reaction step I synthesized N-substituted substrates with procedures from the literature. I used these products and reacted them with chlorobenzene and [Ru(p-cimen)Cl$_2$]$_2$ catalyst. With the purpose of optimization, I changed the solvents and added ligands KOPiv and PPh$_3$. I found out that the best solvent is water and that there is no need to add ligands. Different functional groups influence the ration of mono- and diarylated products.

• Keywords: N-functionalized 2-phenylimidazole, C–H functionalization, directing group, ruthenium catalyst